Regioselective, stereoselective, and conformationally controlled synthesis of (η4-tetraarylcyclobutadiene)(η5-carbomethoxycyclopentadienyl)cobalt metallocenes

Cassar, Doyle J., Nagaradja, Elisabeth, Butler, David C. D., Villemin, Didier and Richards, Christopher J. ORCID: https://orcid.org/0000-0001-7899-4082 (2012) Regioselective, stereoselective, and conformationally controlled synthesis of (η4-tetraarylcyclobutadiene)(η5-carbomethoxycyclopentadienyl)cobalt metallocenes. Organic Letters, 14 (3). pp. 894-897. ISSN 1523-7060

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Abstract

The Friedel–Crafts reaction of (η4-tetraphenylcyclobutadiene)(η5-carbomethoxycyclopentadienyl)cobalt with acid chlorides/aluminum chloride resulted exclusively in para-phenyl acylation. Both monoacylated (1.1 equiv of RCOCl/AlCl3) and tetraacylated products (>4 equiv of RCOCl/AlCl3) were synthesized. Reaction of PhCC(o-RC6H4) (R = Me, i-Pr) with Na(C5H4CO2Me) and CoCl(PPh3)3 gave predominantly (η4-1,3-diaryl-2,4-diphenylcyclobutadiene)(η5-carbomethoxycyclopentadienyl)cobalt metallocenes (1,3-[trans] vs 1,2-[cis] selectivity up to 6:1). Conformational control of Friedel–Crafts reactions on the major isomers gave exclusively para-acylation of the unsubstituted phenyl groups.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	Users 2731 not found.
Date Deposited:	13 Mar 2012 16:14
Last Modified:	24 Sep 2024 08:53
URI:	https://ueaeprints.uea.ac.uk/id/eprint/38204
DOI:	10.1021/ol203415r

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